Synthesis of 10-Oxa-11-deoxyprostaglandin E_1
スポンサーリンク
概要
- 論文の詳細を見る
Synthesis of 10-oxa-11-deoxyprostaglandin E_1 (2b) and related compounds (2a, 17b, and 20) was successfully accomplished starting from nonanedioic acid (3). Decarboxylation of 3,3-di-tert-butoxycarbonyl-2-(6-methoxycarbonyl) hexyl-4-butanolide (6) by heating gave predominantly trans-3-carboxy-2-(6-methoxycarbonyl) hexyl-4-butanolide (7a). Conversion of 7a into the hydroxymethyl lactone (13) and the Pfitzner-Moffatt oxidation of 13 provided trans-3-formyl-2-(6-methoxycarbonyl) hexyl-4-butanolide (14) which served as a key intermediate. The Wittig reaction of 14 with dimethyl 2-oxoheptylphosphonate gave enone (15) which was converted to 10-oxa-11-deoxy PGE_1 methyl ester (16b) by NaBH_4 reduction. Alkaline hydrolysis of 16b and relactonization of the resulting diacid (17b) gave 2b as crystals in a good yield.
- 社団法人日本薬学会の論文
- 1979-03-25
著者
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石田 昭彦
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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和田 征夫
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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日水 順一
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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野口 勝通
田辺製薬株式会社有機化学研究所
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西條 成良
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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野口 勝通
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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高市 雄之
Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.
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和田 征夫
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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西條 成良
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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高市 雄之
Research Laboratory of Drug Metabolism, Tanabe Seiyaku Co., Ltd.,
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日水 順一
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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高市 雄之
Research Laboratory Of Drug Metabolism Tanabe Seiyaku Co. Ltd.
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高市 雄之
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.
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野口 勝通
Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd. :(present Address)sapporo Branch Tanab
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